Microperoxidase 8 catalysed nitrogen oxides formation from oxidation of n-hydroxyguanidines by hydrogen peroxide

European Journal of Biochemistry

Volumn 270, Issue 1, 2003, Pages 47-55

  Ricoux, Rémy ^a   Boucher, Jean Luc ^b   Mandon, Dominique ^c   Frapart, Yves Michel ^b   Henry, Yann ^d   Mansuy, Daniel ^b   Mahy, Jean Pierre ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

^c Institut Le Bel   (France)

^d INSTITUT CURIE   (France)

Author keywords

Iron nitrosyl complexes; Microperoxidase 8; N hydroxyguanidines; Nitric oxide; Nitric oxide synthase

Indexed keywords

2 (4 CARBOXYPHENYL) 4,4,5,5 TETRAMETHYLIMIDAZOLINE 1 OXYL 3 OXIDE; CYANAMIDE; GUANIDINE DERIVATIVE; HYDROGEN PEROXIDE; IMIDAZOLINE DERIVATIVE; N DELTA CYANOORNITHINE; N(G) HYDROXYARGININE; NITRATE; NITRIC OXIDE; NITRITE; PEROXIDASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ELECTRON SPIN RESONANCE; HORSE; INCUBATION TIME; NITRIFICATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SPECTROSCOPY; ULTRAVIOLET RADIATION;

ARGININE; BENZOATES; CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; GUANIDINES; HYDROGEN PEROXIDE; IMIDAZOLES; NITRIC OXIDE; OXIDATION-REDUCTION; PEROXIDASES; SPECTROPHOTOMETRY, ULTRAVIOLET; TEMPERATURE;

EQUUS CABALLUS; MAMMALIA;

EID: 0037217551     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1033.2003.03358.x     Document Type: Article

References (43)

1. Kerwin, J.F., Lancaster, J.R. & Feldman, P.L. (1995) Nitric oxide: A new paradigm for second messengers. J. Med. Chem. 38, 4343-4362.
2. Pfeiffer, S., Mayer, B. & Hemmens, B. (1999) Nitric oxide: Chemical puzzles posed by a biological messenger. Angew. Chem. Int. Ed. Engl. 38, 1714-1731.
3. Moncada, S. & Higgs, E.A. (1995) Molecular mechanisms and therapeutic strategies related to nitric oxide. FASEB J. 9, 1319-1330.
4. Davis, K.L., Martin, E., Turko, I.V. & Murad, F. (2001) Novel effects of nitric oxide. Annu. Rev. Pharmacol. Toxicol. 41, 203-236.
5. Förstermann, U., Gath, I., Schwarz, P., Closs, E.I. & Kleinert, H. (1995) Isoforms of nitric oxide synthase. Properties, cellular distribution and expressional control. Biochem. Pharmacol. 50, 1321-1332.
6. Stuehr, D.J., Kwon, N.S., Nathan, C.F., Griffith, O.W., Feldman, P.L. & Wiseman, J. (1991) Nω-hydroxy-L-arginine is an intermediate in the biosynthesis of nitric oxide from L-arginine. J. Biol. Chem. 296, 6259-6263.
7. G-hydroxy-L-arginine and hydrogen peroxide by neuronal nitric oxide synthase: Implications for mechanism. Biochemistry 36, 14465-14473.
8. Rusche, K.M., Spiering, M.M. & Marletta, M.A. (1998) Reactions catalysed by tetrahydrobiopterin-free nitric oxide synthase. Biochemistry 37, 15503-15512.
9. Moali, C., Boucher, J.L., Renodon-Corniere, A., Stuehr, D.J. & Mansuy, D. (2001) Oxidations of Nω-hydroxyarginine analogues and various N-hydroxyguanidines by NO synthase II: Key role of tetrahydrobiopterin in the reaction mechanism and substrate selectivity. Chem. Res. Toxicol. 14, 202-210.
10. Clement, B., Schultze Mosgau, M.H. & Wohlers, H. (1993) Cytochrome P-450-dependent N-hydroxylation of a guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of the N-hydroxyguanidine metabolite to the urea derivative. Similarity with the oxidation of arginine to citrulline and nitric oxide. Biochem. Pharmacol. 46, 2249-2267.
11. Jousserandot, A., Boucher, J.L., Henry, Y., Niklaus, B., Clement, B. & Mansuy, D. (1998) Microsomal cytochrome P450 dependent oxidation of N-hydroxyguanidines, amidoximes and ketoximes: Mechanism of the oxidative cleavage of their C=N (OH) bond with formation of nitrogen oxides. Biochemistry 37, 17179-17191.
12. Clement, B., Boucher, J.L., Mansuy, D. & Harsdorf, A. (1999) Microsomal formation of nitric oxide and cyanamides from non-physiological N-hydroxyguanidines: N-hydroxydebrisoquine as a model substrate. Biochem. Pharmacol. 58, 439-445.
13. G-hydroxy-L-arginine to nitric oxide mediated by respiratory burst: An alternative pathway to NO synthesis. FEBS Lett. 401, 123-126.
14. Sennequier, N., Boucher, J.L., Battioni, P. & Mansuy, D. (1995) Superoxide anion efficiently performs the oxidative cleavage of C=NOH bonds of amidoximes and N-hydroxyguanidines with formation of nitrogen oxides. Tetrahedron Lett. 36, 6059-6062.
15. Fukuto, J., Wallace, G.C., Hszieh, R. & Chaudhrui, G. (1992) Chemical oxidation of N-hydroxyguanidine compounds. Release of nitric oxide, nitroxyl and possible relationship to the mechanism of biological nitric oxide generation. Biochem. Pharmacol. 43, 607-613.
16. Fukuto, J., Stuehr, D., Feldman, P.L., Bova, M.P. & Wong, P. (1993) Peracid oxidation of an N-hydroxyguanidine compound: A chemical model for the oxidation of Nω-hydroxy-L-arginine by nitric oxide synthase. J. Med. Chem. 36, 2666-2670.
17. Yoo, J. & Fukuto, J.M. (1995) Oxidation of N-hydroxyguanidine by nitric oxide and the possible generation of vasoactive species. Biochem. Pharmacol. 50, 1995-2000.
18. Boucher, J.L., Genet, A., Vadon, S., Delaforge, M. & Mansuy, D. (1992) Formation of nitrogen oxides and citrulline upon oxidation of Nω-hydroxy-L-arginine by hemeproteins. Biochem. Biophys. Res. Commun. 184, 1158-1164.
19. Hirst, J. & Goodin, D.B. (2000) Unusual oxidative chemistry of Nω-hydroxyarginine and N-hydroxyguanidine catalysed at an engineered cavity in a heme peroxidase. J. Biol. Chem. 275, 8582-8591.
20. Aron, J., Baldwin, D.A., Marques, H., Pratt, J.M. & Adams, P.A. (1986) Hemes and hemoproteins 1: Preparation and analysis of heme containing octapeptide (microperoxidase 8) and identification of the monomeric form in aqueous solution. J. Inorg. Biochem. 27, 227-243.
21. Baldwin, D.A., Marques, H. & Pratt, J.M. (1987) Hemes and hemoproteins 5: Kinetics of the peroxidasic activity of micro-peroxidase 8, model for the peroxidase enzymes. J. Inorg. Biochem. 30, 203-217.
22. Marques, H.M., Shongwe, M.S., Munro, O.Q. & Egan, T.J. (1997) The haempeptides from cytochrome c. Exploring the basic chemistry of the iron porphyrins and modelling aspects of the haemoproteins. S. Afr. Tydskr. Chem. 50, 166-180.
23. Casella, L., De Gioia, L., Silvestri, G.F., Monzani, E., Redaelli, C., Roncone, R. & Santagostini, L. (2000) Covalently modified microperoxidases as heme-peptide models for peroxidases. J. Inorg. Biochem. 79, 31-40.
24. 2-catalysed aromatic hydroxylation proceeds by a cytochrome-P450-type oxygen transfer reaction mechanism. Eur. J. Biochem. 240, 232-238.
25. Boersma, M.G., Primus, J.L., Koerts, J., Veeger, C. & Rietjens, I.M. (2000) Heme-(hydro) peroxide mediated O- and N-deal-kylation. A study with microperoxidase. Eur. J. Biochem. 267, 6673-6678.
26. Lefevre-Groboillot, D., Dijols, S., Boucher, J.L., Mahy, J.P., Ricoux, R., Desbois, A., Zimmermann, J.L. & Mansuy, D. (2001) N-hydroxyguanidines as new heme ligands: UV-Visible, EPR, and resonance Raman studies of the interaction of various compounds bearing a C=NOH function with microperoxidase-8. Biochemistry 40, 9909-9917.
27. Primus, J.-L., Boersma, M.G., Mandon, D., Boeren, S., Veeger, C., Weiss, R. & Rietjens I.M.C.M. (1999) The effect of iron to manganese substitution on microperoxidase 8 catalysed peroxidase and cytochrome P450 type of catalysis. J. Bioinorg. Chem. 4, 274-283.
28. Munro, O.Q. & Marques, H.M. (1996) Heme-peptide models for hemoproteins. Solution chemistry of N-acetylmicroperoxidase 8. Inorg. Chem. 35, 3752-3767.
29. Schantl, J.G. & Türk, W. (1989) 1-(4-chlorophenyl)-3-hydroxyguanidine and O-acyl-derivatives. Sci. Pharm. 57, 375-380.
30. Feelisch, M., Kubitzer, D. & Werringloer, J. (1996) The Oxy-hemoglobin Assay. In Methods in Nitric Oxide Research (Feelisch, M. & Stamler, J.S., eds), pp. 455-478. J. Wiley and Sons Ltd, Chichester, UK.
31. 15N]nitrate in biological fluids. Anal. Biochem. 126, 131-138.
32. Verdon, C.P., Burton, B.A. & Prior, R.L. (1995) Sample pretreatment with nitrate reductase and glucose-6-phosphate dehydrogenase quantitatively reduces nitrate while avoiding interferences by NADP when the Griess reaction is used to assay for nitrite. Anal. Biochem. 224, 502-508.
33. Akaike, T., Yoshida, M., Miyamoto;, Y., Sato, K., Kohno, M., Sasamoto, K., Miyazaki, K., Ueda, S. & Maeda, H. (1993) Antagonistic action of imidazolineoxyl N-oxides against endothelium-derived relaxing factor/NO through a radical reaction. Biochemistry 32, 827-832.
34. Wang, J.S., Baek, H.K. & Van Wart, H.E. (1991) High-valent intermediates in the reaction of N-acetylmicroperoxidase 8 with hydrogen peroxide: Models for compounds 0, I and II of horse-radish peroxidase. Biochem. Biophys. Res. Commun. 179, 1320-1324.
35. Ignarro, L.J., Fukuto, J.M., Griscavage, J.M., Rogers, N.E. & Byrns, R.E. (1993) Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate: Comparison with enzymatically formed nitric oxide from L-arginine. Proc. Natl Acad. Sci. USA 90, 8103-8107.
36. Stamler, J.S., Singel, D.J. & Loscalzo, J. (1992) Biochemistry of nitric oxide and its redox-activated forms. Science 258, 1898-1902.
37. Boucher, J.L., Vadon, S., Tomas, A., Viossat, B. & Mansuy, D. (1996) Oxidation of arylamidoximes by hydrogen peroxide and horseradish peroxidase in water: Easy preparation and first X-ray structure of O-(arylimidoyl) arylamidoximes. Tetrahedron Lett. 37, 3113-3116.
38. Vadon LeGoff, S., Boucher, J.L. & Mansuy, D. (2000) Oxidation of arylamidoximes by various chemical and biomimetic systems: Comparison with their oxidation by hemeproteins. C.R. Acad. Sci. Paris, Serie IIC 3, 785-792.
39. Gilchrist, T.L., Harris, C.J., Hawkins, D.G., Moody, C.J. & Rees, C.W. (1976) Synthesis of 1H-1,2,4-triazole 2-oxides and annelated derivatives. J. Chem. Soc. Perkin I, 2166-2170.
40. Renodon-Corniére, A., Boucher, J.L., Dijols, S., Stuehr, D.J. & Mansuy, D. (1999) Efficient formation of nitric oxide from selective oxidation of N-aryl N′-hydroxyguanidines by inducible nitric oxide synthase. Biochemistry 38, 4663-4668.
41. Bailey, D.M., DeGrazia, C.G., Lape, H.E., Frering, R., Fort, D. & Skulan, T. (1973) Hydroxyguanidines. A new class of anti-hypertensive agents. J. Med. Chem. 16, 151-156.
42. Abdul-Hussain, M.N., Jia, Y.L. & Hussain, S.N.A. (1996) Mechanisms mediating the vasodilatory effects of N-hydroxy-L-arginine in coronary arteries. Eur. J. Pharmacol. 305, 155-161.
43. Everett, S.A., Smith, K.A., Patel, K.B., Dennis, M.F., Stratford, M.R.L. & Wardman, P. (1996) The involvement of nitric oxide in the toxicity of hydroxyguanidine in leukaemia HL60 cells. Br. J. Cancer 74, S172-S176.